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This paper delves in to the life of Grigory Vinsky, a Ukrainian nobleman and member of Catherine II's guards’ regiment, whose exile to Bashkiria and subsequent autobiography offer unique insights into Enlightenment culture and the personal dimensions of living under autocracy. Vinsky's experiences and reflections provide a valuable ego-document that enriches our understanding of individual subjecthood, the cultural milieu of the Enlightenment, and the intricate relationship between autocratic power, mercy, and the emotional lives of Imperial subjects.